Talking Derby Hats with the Hat Designers

By Jessica Alyea

Part 2 — Lisa Lake-Roedemein & Helen Overfield

Kentucky Derby Festival princess Andi Dahmer is wearing: Hat by Hats Off! By Helen, $155; Earrings available at Davis Jewelers, $240. 
Photos by Melissa Donald

Hat designers from near and far send us their best creations for our Derby issue. We asked these experts the hat questions you need to know to put your best brim forward this Derby season.

The designers:
Lisa Lake-Roedemein founded Madam Foo Foo Couture in 2009 as a labor of her love for fashion and horses. A portion of profits from her hat creations go toward Thoroughbred retirement, retraining, and rescue. She lives and works in Kentucky, and her designs are available in Louisville at Rodes for Her, Rodeo Drive, Merci Boutique and the Brown Hotel.

Helen Overfield started Hats Off by Helen in 2014, but she’s been ‘unofficially’ creating hats for more than 25 years. She gives each of her handcrafted Kentucky creations a Derby-related name, such as “Legacy Lily,” “Pink in the Paddock,” “Southern Sweetie,” or “Go Big or Go Home,” and each hat comes with two betting numbers for the wearer to try her luck with.

Do you have any hair suggestions for certain hats?
Lisa: I like the romantic, side-swept ponytail worn with large hats.
Helen: Many women do ponytails or side ponytails. If you have bangs, it's best to wear them under the brim of your hat. The hat is your focal point. Don't overdo the hairstyle and accessories.

Fascinator by Madam Foo Foo, $390.

What trends are hot this year?
Lisa: While fascinators are still popular, many women are returning to the traditional hat with a large brim.
Helen: Feathers, flowers, and netting. Bold colors and colors that complement — think “a pop of color” versus “matchy-matchy.”

How do height and size play into hat choice?
Helen: It is all about scale and proportion. Someone with smaller features can wear smaller-brimmed hats better than a person with larger features, while wider-brim hats tend to look better on women with larger features. But it really is best to look in the mirror — you can immediately see if it is complementing the shape of your face or detracting from it.

What is your best advice for wearing or buying a hat?
Helen: Wear something comfortable that makes you feel confident. That is the most important thing. Don’t wear a tight fascinator that hurts your head so much that you need to drink another mint julep just to endure the fashion. Keep in mind that wide-brimmed hats can run in various sizes, so if you need hat tape to make it smaller, or to have it stretched out, it is best to think of that before you are en route to the track! Often the location of your seats will determine the style of hat you wear. In the infield or grandstand, a more casual hat will be fine. On Millionaire's Row or in the Mansion or Clubhouse, a more formal hat is de rigueur.

Find more hat advice in Part 1 of this series.